36374-82-0

Basic information

• Product Name: 1-Iodo-2-methylnaphthalene
• Synonyms: 1-Iodo-2-methylnaphthalene
• CAS NO: 36374-82-0
• Molecular Formula: C₁₁H₉I
• Molecular Weight: 268.09363
• Mol File: 36374-82-0.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 155 °C
• Appearance: /
• Density: 1.655±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 1-Iodo-2-methylnaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Iodo-2-methylnaphthalene(36374-82-0)
• EPA Substance Registry System: 1-Iodo-2-methylnaphthalene(36374-82-0)

Safety Data

• Hazardous Substances Data: 36374-82-0(Hazardous Substances Data)

Usage

Type of compound

Halogenated derivative of 2-methylnaphthalene (a polycyclic aromatic hydrocarbon)

Uses

Intermediate in organic synthesis (e.g. production of pharmaceuticals and agrochemicals), reagent in chemical reactions (e.g. preparation of substituted naphthalenes and other aromatic compounds)

Physical properties

Colorless to pale yellow solid at room temperature, sparingly soluble in water, soluble in organic solvents (e.g. ether, chloroform)

Safety concerns

Toxic and potentially harmful to human health and the environment

Upstream product

• 2586-62-1 1-bromo-2-methylnaphtalene 
• 91-57-6 2-Methylnaphthalene 
• 21450-90-8 (2-methyl-1-naphthyl)magnesium bromide 
• 1575-96-8 2-methyl-1-naphthoic acid 
• 2246-44-8 1-amino-2-methylnaphthalene 

Downstream Products

• 93948-24-4 2,6-Dimethyl-1-(naphth-2-yl-methyl)-piperidin 
• 91-57-6 2-Methylnaphthalene 
• 130247-11-9 1-<2-(benzyloxycarbonyl)-2-<(tert-butoxycarbonyl)amino>ethenyl>-2-methylnaphthalene 
• 60536-98-3 2,2'-dimethyl-1,1'-binaphthyl 
• 19634-89-0 (R)-2,2'-dimethyl-1,1'-binaphthyl 
• 32587-64-7 (S)-(+)-2,2'-dimethyl-1,1'-binaphthyl 
• 20944-85-8 2-methyl-1-naphthonitrile 
• 19634-89-0 (S)-(+)-2,2'-dimethyl-1,1'-binaphtyl 
• 143088-47-5 1-Heptyltellanyl-4-methyl-benzene 
• 793724-78-4 2-(2-methyl-[1]naphthyl)-benzoic acid 

Relevant articles and documents

Application of a Ferrocene-Based Palladacycle Precatalyst to Enantioselective Aryl-Aryl Kumada Coupling

The palladium catalysed reaction of 1-iodo-2-methylnaphthalene and 2-methyl-1-naphthylmagnesium bromide gave quantitatively an (Sa)-configured cross-coupled product in 80 % e.e. using (R,Sp)-PPFA as a ligand. N,N-Dimethylaminomethylferrocene was cyclopalladated (Na2PdCl4, (S)?Ac?Phe?OH, 93 % e.e., as determined by 1H NMR as a result of self-induced non-equivalence), and the resulting (Sp)-configured dimeric palladacycle was employed as a precatalyst for this cross-coupling reaction (5 mol%). Addition to the palladacycle of diphenylphosphine and subsequent base-promoted bidentate ligand synthesis and palladium capture gave an in situ generated catalyst resulting in an (Sp)-configured product in up to 71 % e.e.

An Unprecedented, Lewis Acid-Mediated, Metal-Free Iodoannulation Strategy to Aromatic Iodides

A direct transformation of ortho-alkynylated aromatic vinyl ethers to 1-iodonaphthalenes and other iodo-heterocycles under mild Lewis acidic conditions in the presence of iodide as an external nucleophile is reported. The first example of an iodoannulation strategy using a nucleophilic source of iodine, coupled with good to excellent yields, exclusive alpha regioselectivity and a broad substrate scope makes this work an attractive avenue towards the construction of aromatic iodides.

Efficient and direct iodination of alkyl benzenes using polymer/HIO4 and I2 under mild condition

An efficient and rapid method has been found for the iodination of aromatic compounds using iodine and polymer-supported periodic acid (PSPIA) as an oxidant under mild aprotic conditions. The reagent after the completion of the reaction was easily removed by filtration and was regenerated for further use. This method has some advantages such as: mild reaction conditions, straight forward procedure, inexpensive method, high yields and one-pot conversion.